# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ekdoa
_database_code_depnum_ccdc_archive 'CCDC 2017463'
loop_
_audit_author_name
_audit_author_address
'Matthew Polson'
;School of Physical and Chemical Sciences, University of Canterbury, Christchurch
New Zealand
;
_audit_update_record             
;
2020-09-10 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl2 Cu N4 O12'
_chemical_formula_weight         596.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8276(15)
_cell_length_b                   8.1623(12)
_cell_length_c                   10.464(2)
_cell_angle_alpha                90.864(15)
_cell_angle_beta                 99.515(17)
_cell_angle_gamma                93.963(16)
_cell_volume                     573.55(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    280.00(10)
_cell_measurement_reflns_used    1876
_cell_measurement_theta_min      3.8440
_cell_measurement_theta_max      28.8270

_exptl_crystal_description       prism
_exptl_crystal_colour            blue-green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             305
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    1.256
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.437
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      280.00(10)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            4052
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.332
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4052
_reflns_number_gt                2869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1194P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4052
_refine_ls_number_parameters     208
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1707
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
CU1 Cu -0.500000 0.500000 0.500000 0.0338(3) Uani 1 2 d S . P . .
N1 N -0.2014(5) 0.4988(4) 0.4995(3) 0.0260(7) Uani 1 1 d . . . . .
C2 C -0.0912(6) 0.3904(5) 0.5682(4) 0.0329(10) Uani 1 1 d . . . . .
H2 H -0.151618 0.313081 0.616320 0.040 Uiso 1 1 calc R U . . .
C3 C -0.1096(6) 0.6075(5) 0.4318(4) 0.0322(10) Uani 1 1 d . . . . .
H3 H -0.183409 0.683754 0.383497 0.039 Uiso 1 1 calc R U . . .
N11 N -0.3469(6) 0.6480(5) 0.8075(4) 0.0457(10) Uani 1 1 d . . . . .
H11 H -0.389(8) 0.704(7) 0.746(6) 0.055 Uiso 1 1 d . U . . .
C12 C -0.3802(6) 0.4836(5) 0.7881(4) 0.0337(10) Uani 1 1 d . . . . .
O12 O -0.4622(5) 0.4237(4) 0.6762(3) 0.0368(7) Uani 1 1 d . . . . .
C13 C -0.3204(7) 0.3834(6) 0.8948(4) 0.0362(10) Uani 1 1 d . . . . .
C14 C -0.2418(7) 0.4598(7) 1.0115(5) 0.0471(12) Uani 1 1 d . . . . .
H14 H -0.205270 0.395782 1.083122 0.057 Uiso 1 1 calc R U . . .
C15 C -0.2151(8) 0.6294(7) 1.0261(5) 0.0542(14) Uani 1 1 d . . . . .
H15 H -0.162658 0.677941 1.106543 0.065 Uiso 1 1 calc R U . . .
C16 C -0.2651(8) 0.7220(7) 0.9242(6) 0.0542(14) Uani 1 1 d . . . . .
H16 H -0.244759 0.835763 0.932074 0.065 Uiso 1 1 calc R U . . .
C17 C -0.3489(9) 0.2019(7) 0.8750(5) 0.0535(13) Uani 1 1 d . . . . .
H17A H -0.259548 0.166489 0.820100 0.064 Uiso 1 1 calc R U . . .
H17B H -0.483747 0.171900 0.835017 0.064 Uiso 1 1 calc R U . . .
H17C H -0.321716 0.150291 0.957279 0.064 Uiso 1 1 calc R U . . .
O1W O -0.4536(6) 0.7975(5) 0.5666(4) 0.0515(9) Uani 1 1 d D . . . .
H1WA H -0.544(7) 0.856(6) 0.579(5) 0.062 Uiso 1 1 d D U . . .
H1WB H -0.366(7) 0.862(6) 0.548(5) 0.062 Uiso 1 1 d D U . . .
CL1 Cl 0.1217(2) 0.93269(15) 0.70919(13) 0.0540(4) Uani 1 1 d . . . . .
O1 O -0.008(3) 0.807(2) 0.6718(19) 0.099(7) Uani 0.434(12) 1 d . . P A 1
O2 O 0.2940(19) 0.878(2) 0.7943(12) 0.107(6) Uani 0.434(12) 1 d . . P A 1
O3 O 0.065(3) 1.0733(14) 0.7428(16) 0.111(7) Uani 0.434(12) 1 d . . P A 1
O4 O 0.262(3) 1.007(2) 0.6491(18) 0.065(4) Uani 0.434(12) 1 d . . P A 1
O1' O 0.095(3) 0.7601(15) 0.7103(15) 0.092(5) Uani 0.566(12) 1 d . . P A 2
O2' O 0.1487(19) 0.9921(14) 0.8425(9) 0.107(5) Uani 0.566(12) 1 d . . P A 2
O3' O -0.0826(13) 0.9861(15) 0.6601(11) 0.098(4) Uani 0.566(12) 1 d . . P A 2
O4' O 0.221(2) 0.9683(19) 0.5928(14) 0.068(3) Uani 0.566(12) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CU1 O12 1.937(3) 2_466 ?
CU1 O12 1.937(3) . ?
CU1 N1 2.040(3) . ?
CU1 N1 2.040(3) 2_466 ?
N1 C3 1.331(5) . ?
N1 C2 1.341(5) . ?
C2 C3 1.370(5) 2_566 ?
C2 H2 0.9300 . ?
C3 C2 1.370(5) 2_566 ?
C3 H3 0.9300 . ?
N11 C12 1.352(6) . ?
N11 C16 1.369(7) . ?
N11 H11 0.82(6) . ?
C12 O12 1.285(5) . ?
C12 C13 1.415(6) . ?
C13 C14 1.372(7) . ?
C13 C17 1.488(7) . ?
C14 C15 1.386(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.328(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1W H1WA 0.83(3) . ?
O1W H1WB 0.82(3) . ?
CL1 O3 1.297(10) . ?
CL1 O1 1.317(14) . ?
CL1 O4 1.34(2) . ?
CL1 O1' 1.408(13) . ?
CL1 O2' 1.449(9) . ?
CL1 O2 1.454(11) . ?
CL1 O3' 1.501(9) . ?
CL1 O4' 1.512(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 CU1 O12 180.00(18) 2_466 . ?
O12 CU1 N1 89.86(13) 2_466 . ?
O12 CU1 N1 90.14(13) . . ?
O12 CU1 N1 90.14(13) 2_466 2_466 ?
O12 CU1 N1 89.86(13) . 2_466 ?
N1 CU1 N1 180.0 . 2_466 ?
C3 N1 C2 117.9(3) . . ?
C3 N1 CU1 120.7(3) . . ?
C2 N1 CU1 121.4(3) . . ?
N1 C2 C3 120.7(4) . 2_566 ?
N1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 2_566 . ?
N1 C3 C2 121.4(4) . 2_566 ?
N1 C3 H3 119.3 . . ?
C2 C3 H3 119.3 2_566 . ?
C12 N11 C16 123.9(5) . . ?
C12 N11 H11 116(4) . . ?
C16 N11 H11 120(4) . . ?
O12 C12 N11 120.1(4) . . ?
O12 C12 C13 122.5(4) . . ?
N11 C12 C13 117.3(4) . . ?
C12 O12 CU1 136.0(3) . . ?
C14 C13 C12 117.9(4) . . ?
C14 C13 C17 123.6(5) . . ?
C12 C13 C17 118.5(4) . . ?
C13 C14 C15 122.1(5) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C16 C15 C14 119.5(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 N11 119.3(5) . . ?
C15 C16 H16 120.4 . . ?
N11 C16 H16 120.4 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H1WA O1W H1WB 105(6) . . ?
O3a CL1 O1 121.4(13) . . ?
O3a CL1 O4 91.4(11) . . ?
O1a CL1 O4 130.6(11) . . ?
O1'b CL1 O2' 107.2(8) . . ?
O3a CL1 O2 114.5(11) . . ?
O1a CL1 O2 110.2(12) . . ?
O4a CL1 O2 82.9(10) . . ?
O1'b CL1 O3' 104.2(8) . . ?
O2'b CL1 O3' 100.3(7) . . ?
O1'b CL1 O4' 104.7(9) . . ?
O2'b CL1 O4' 136.0(8) . . ?
O3'b CL1 O4' 100.2(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 C3 0.0(6) . . . 2_566 ?
CU1 N1 C2 C3 -179.2(3) . . . 2_566 ?
C2 N1 C3 C2 0.0(6) . . . 2_566 ?
CU1 N1 C3 C2 179.2(3) . . . 2_566 ?
C16 N11 C12 O12 178.3(4) . . . . ?
C16 N11 C12 C13 -2.0(7) . . . . ?
N11 C12 O12 CU1 20.1(6) . . . . ?
C13 C12 O12 CU1 -159.6(3) . . . . ?
O12 C12 C13 C14 -177.3(4) . . . . ?
N11 C12 C13 C14 3.0(6) . . . . ?
O12 C12 C13 C17 1.7(7) . . . . ?
N11 C12 C13 C17 -177.9(4) . . . . ?
C12 C13 C14 C15 -1.8(7) . . . . ?
C17 C13 C14 C15 179.2(5) . . . . ?
C13 C14 C15 C16 -0.6(8) . . . . ?
C14 C15 C16 N11 1.7(8) . . . . ?
C12 N11 C16 C15 -0.4(8) . . . . ?

_refine_diff_density_max         1.458
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.113


_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vsa
_database_code_depnum_ccdc_archive 'CCDC 2017464'
loop_
_audit_author_name
_audit_author_address
'Louise N. Dawe'
;Wilfrid Laurier University
Canada
;
_audit_update_record             
;
2020-07-19 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
; catena-diaqua-bis(6-methyl-2-pyridone)(u/-pyrazine)copper(II) perchlorate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl2 Cu N4 O12'
_chemical_formula_weight         596.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   23.016(11)
_cell_length_b                   6.822(3)
_cell_length_c                   7.656(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.189(8)
_cell_angle_gamma                90
_cell_volume                     1202.1(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1992
_cell_measurement_theta_min      3.1146
_cell_measurement_theta_max      30.4755

_exptl_crystal_description       Prism
_exptl_crystal_colour            'Light Green'
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.410
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             610
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.198
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.7581
_exptl_absorpt_correction_T_min  0.6187
_exptl_absorpt_process_details   '(T. Higashi, 2000)'
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Sealed Tube'
_diffrn_measurement_device_type  'Saturn70 (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6233
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         30.207
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measured_fraction_theta_full 0.938
_reflns_number_total             1686
_reflns_number_gt                1670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+1.8123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1686
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.000000 0.000000 0.000000 0.01690(15) Uani 1 4 d S T P . .
N1 N 0.000000 -0.2965(3) 0.000000 0.0168(4) Uani 1 2 d S T P . .
C2 C -0.02277(7) -0.3984(2) 0.1329(2) 0.0192(3) Uani 1 1 d . . . . .
H2 H -0.039231 -0.330108 0.228853 0.023 Uiso 1 1 calc R U . . .
N11 N 0.14622(10) 0.000000 0.0343(3) 0.0255(4) Uani 1 2 d S T P . .
H11 H 0.1214(16) 0.000000 0.123(5) 0.031 Uiso 1 2 d S U P . .
C12 C 0.12298(11) 0.000000 -0.1287(3) 0.0213(4) Uani 1 2 d S T P . .
O12 O 0.06813(8) 0.000000 -0.1515(2) 0.0216(3) Uani 1 2 d S T P . .
C13 C 0.16268(12) 0.000000 -0.2693(4) 0.0309(6) Uani 1 2 d S T P . .
H13 H 0.148895 0.000000 -0.386446 0.037 Uiso 1 2 calc R U P . .
C14 C 0.22121(13) 0.000000 -0.2354(5) 0.0381(7) Uani 1 2 d S T P . .
H14 H 0.247729 0.000000 -0.330201 0.046 Uiso 1 2 calc R U P . .
C15 C 0.24275(13) 0.000000 -0.0646(5) 0.0372(7) Uani 1 2 d S T P . .
H15 H 0.283448 0.000000 -0.043459 0.045 Uiso 1 2 calc R U P . .
C16 C 0.20456(12) 0.000000 0.0717(4) 0.0329(6) Uani 1 2 d S T P . .
C17 C 0.22043(17) 0.000000 0.2610(5) 0.0473(9) Uani 1 2 d S T P . .
H17A H 0.2038(14) -0.108(6) 0.317(4) 0.057 Uiso 1 1 d . U . . .
H17C H 0.256(2) 0.000000 0.271(7) 0.057 Uiso 1 2 d S U P . .
O1W O 0.05612(9) 0.000000 0.2756(3) 0.0272(4) Uani 1 2 d S T P . .
H1W H 0.0590(12) 0.089(4) 0.339(4) 0.033 Uiso 1 1 d . U . . .
Cl1 Cl 0.39243(3) 0.000000 -0.41446(8) 0.02683(18) Uani 1 2 d S T P . .
O1 O 0.38681(12) 0.000000 -0.2287(3) 0.0515(7) Uani 1 2 d S T P A .
O2 O 0.42515(14) 0.1657(3) -0.4698(3) 0.0785(9) Uani 1 1 d . . . . .
O3 O 0.33842(14) 0.0564(7) -0.4926(5) 0.0613(18) Uani 0.5 1 d . . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O12 1.9536(19) 5 ?
Cu1 O12 1.9536(19) . ?
Cu1 N1 2.023(2) . ?
Cu1 N1 2.023(2) 5 ?
Cu1 O1W 2.470(2) . ?
N1 C2 1.3404(19) . ?
N1 C2 1.3404(19) 2 ?
C2 C2 1.386(3) 6_545 ?
C2 H2 0.9500 . ?
N11 C12 1.357(3) . ?
N11 C16 1.372(4) . ?
N11 H11 0.89(4) . ?
C12 O12 1.274(3) . ?
C12 C13 1.414(4) . ?
C13 C14 1.371(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.367(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.494(5) . ?
C17 H17A 0.93(4) . ?
C17 H17C 0.83(5) . ?
C17 H17A 0.93(4) 6 ?
O1W H1W 0.78(3) . ?
O1W H1W 0.78(3) 6 ?
Cl1 O2 1.424(2) 6 ?
Cl1 O2 1.424(2) . ?
Cl1 O1 1.429(2) . ?
Cl1 O3 1.431(3) 6 ?
Cl1 O3 1.431(3) . ?
O3 O3 0.770(10) 6 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 Cu1 O12 180.00(6) 5 . ?
O12 Cu1 N1 90.0 5 . ?
O12 Cu1 N1 90.0 . . ?
O12 Cu1 N1 90.0 5 5 ?
O12 Cu1 N1 90.0 . 5 ?
N1 Cu1 N1 180.0 . 5 ?
O12 Cu1 O1W 84.91(8) 5 . ?
O12 Cu1 O1W 95.09(8) . . ?
N1 Cu1 O1W 90.0 . . ?
N1 Cu1 O1W 90.0 5 . ?
C2 N1 C2 117.5(2) . 2 ?
C2 N1 Cu1 121.25(10) . . ?
C2 N1 Cu1 121.25(10) 2 . ?
N1 C2 C2 121.26(10) . 6_545 ?
N1 C2 H2 119.4 . . ?
C2 C2 H2 119.4 6_545 . ?
C12 N11 C16 125.1(2) . . ?
C12 N11 H11 117(2) . . ?
C16 N11 H11 118(2) . . ?
O12 C12 N11 120.9(2) . . ?
O12 C12 C13 122.6(2) . . ?
N11 C12 C13 116.5(2) . . ?
C12 O12 Cu1 135.71(17) . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 N11 118.2(3) . . ?
C15 C16 C17 125.8(3) . . ?
N11 C16 C17 116.0(3) . . ?
C16 C17 H17A 110(2) . . ?
C16 C17 H17C 109(4) . . ?
H17A C17 H17C 111(3) . . ?
C16 C17 H17A 110(2) . 6 ?
H17A C17 H17A 104(4) . 6 ?
H17C C17 H17A 111(3) . 6 ?
Cu1 O1W H1W 125(2) . . ?
Cu1 O1W H1W 125(2) . 6 ?
H1W O1W H1W 102(4) . 6 ?
O2 Cl1 O2 105.1(2) 6 . ?
O2 Cl1 O1 110.25(11) 6 . ?
O2 Cl1 O1 110.25(11) . . ?
O2 Cl1 O3 97.0(2) 6 6 ?
O2 Cl1 O3 123.3(2) . 6 ?
O1 Cl1 O3 109.6(2) . 6 ?
O2 Cl1 O3 123.3(2) 6 . ?
O2 Cl1 O3 97.0(2) . . ?
O1 Cl1 O3 109.6(2) . . ?
O3 Cl1 O3 31.2(4) 6 . ?
O3 O3 Cl1 74.4(2) 6 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C2 C2 0.004(0) 2 . . 6_545 ?
Cu1 N1 C2 C2 180.002(1) . . . 6_545 ?
C16 N11 C12 O12 180.0 . . . . ?
C16 N11 C12 C13 0.000(0) . . . . ?
N11 C12 O12 Cu1 0.000(0) . . . . ?
C13 C12 O12 Cu1 180.000(0) . . . . ?
O12 C12 C13 C14 180.000(0) . . . . ?
N11 C12 C13 C14 0.000(0) . . . . ?
C12 C13 C14 C15 0.000(0) . . . . ?
C13 C14 C15 C16 0.000(0) . . . . ?
C14 C15 C16 N11 0.000(0) . . . . ?
C14 C15 C16 C17 180.000(0) . . . . ?
C12 N11 C16 C15 0.000(0) . . . . ?
C12 N11 C16 C17 180.000(0) . . . . ?
O2 Cl1 O3 O3 36.59(14) 6 . . 6 ?
O2 Cl1 O3 O3 149.86(11) . . . 6 ?
O1 Cl1 O3 O3 -95.70(9) . . . 6 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O12 0.95 2.42 2.915(2) 112.1 5 yes
C2 H2 O2 0.95 2.45 3.302(3) 149.1 3_446 yes
N11 H11 O1W 0.89(4) 1.91(4) 2.782(3) 168(4) . yes
C17 H17C O3a 0.83(5) 2.64(5) 3.324(5) 141(4) 1_556 yes
C17 H17C O3a 0.83(5) 2.64(5) 3.324(5) 141(4) 6_556 yes
O1W H1W O2 0.78(3) 1.98(3) 2.756(3) 170(3) 7 yes

_refine_diff_density_max         0.642
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.077

# start Validation Reply Form
_vrf_PLAT029_vsa                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.938 Why?  
RESPONSE: This resulted from physical instrument limitations. While this
is not ideal, the fraction collected is still greater than 90%, and
completeness to 0.71 A resolution is 100%. Further, additional
experimental characterizations agree with the presented model.
;
_vrf_PLAT911_vsa                 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         71 Report
RESPONSE: Some may have been obscured by the beamstop, while others may
be related to the _measured_fraction_theta_full value.
;
_vrf_PLAT913_vsa                 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         14 Note  
RESPONSE: Some may have been obscured by the beamstop, while others may
be related to the _measured_fraction_theta_full value.
;

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ekdi7a
_database_code_depnum_ccdc_archive 'CCDC 2018693'
loop_
_audit_author_name
_audit_author_address
'Matthew Polson'
;Department of Physical and Chemical Sciences, University of Canterbury, Christchurch
New Zealand
;
_audit_update_record             
;
2020-07-23 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl2 Cu N4 O12'
_chemical_formula_weight         596.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   23.0309(19)
_cell_length_b                   6.8184(5)
_cell_length_c                   7.7006(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.399(11)
_cell_angle_gamma                90
_cell_volume                     1209.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    280.0(2)
_cell_measurement_reflns_used    1703
_cell_measurement_theta_min      5.6510
_cell_measurement_theta_max      76.3600

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             610
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    3.927
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      280(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            3789
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.746
_diffrn_reflns_theta_max         76.645
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1333
_reflns_number_gt                1167
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²+0.6302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   Difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1333
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.0395(2) Uani 1 4 d S T P . .
N1 N 0.500000 0.7970(3) 0.500000 0.0385(5) Uani 1 2 d S T P . .
C2 C 0.47665(10) 0.8988(3) 0.6305(3) 0.0413(5) Uani 1 1 d . . . . .
H2 H 0.460090 0.831867 0.723004 0.050 Uiso 1 1 calc R U . . .
N11 N 0.35367(13) 0.500000 0.4577(4) 0.0521(7) Uani 1 2 d S T P . .
H11 H 0.376(2) 0.500000 0.373(6) 0.064(13) Uiso 1 2 d S . P . .
C12 C 0.37662(14) 0.500000 0.6205(4) 0.0452(7) Uani 1 2 d S T P . .
O12 O 0.43104(10) 0.500000 0.6441(3) 0.0458(5) Uani 1 2 d S T P . .
C13 C 0.33640(18) 0.500000 0.7587(6) 0.0640(10) Uani 1 2 d S T P . .
H13 H 0.349264 0.500000 0.873475 0.077 Uiso 1 2 calc R U P . .
C14 C 0.27864(19) 0.500000 0.7208(7) 0.0742(12) Uani 1 2 d S T P . .
H14 H 0.252274 0.500000 0.811734 0.089 Uiso 1 2 calc R U P . .
C15 C 0.25779(19) 0.500000 0.5535(7) 0.0732(12) Uani 1 2 d S T P . .
H15 H 0.218018 0.500000 0.531847 0.088 Uiso 1 2 calc R U P . .
C16 C 0.29630(18) 0.500000 0.4190(6) 0.0638(10) Uani 1 2 d S T P . .
C17 C 0.2809(2) 0.500000 0.2301(7) 0.0884(15) Uani 1 2 d S T P . .
H17A H 0.290823 0.375515 0.180201 0.106 Uiso 0.5 1 calc R U P . .
H17B H 0.301945 0.602157 0.172294 0.106 Uiso 0.5 1 calc R U P . .
H17C H 0.239939 0.522328 0.216378 0.106 Uiso 0.5 1 calc R U P . .
O1W O 0.55412(13) 0.500000 0.7802(4) 0.0572(6) Uani 1 2 d DS T P . .
H1 H 0.5558(12) 0.600(3) 0.838(3) 0.053(8) Uiso 1 1 d D . . . .
Cl1 Cl 0.60847(4) 1.000000 0.91575(12) 0.0564(3) Uani 1 2 d S T P . .
O1 O 0.61402(19) 1.000000 0.7338(5) 0.1073(14) Uani 1 2 d S T P A .
O3 O 0.6665(6) 0.943(4) 0.9932(17) 0.070(5) Uani 0.25 1 d . . P A 1
O2 O 0.5891(4) 0.8218(17) 0.9814(18) 0.097(3) Uani 0.5 1 d . . P A 1
O3A O 0.6525(8) 1.059(9) 0.997(4) 0.168(19) Uani 0.25 1 d . . P A 2
O2A O 0.5654(3) 0.8502(15) 0.9614(14) 0.074(2) Uani 0.5 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O12 1.943(2) . ?
Cu1 O12 1.944(2) 5_666 ?
Cu1 N1 2.025(2) . ?
Cu1 N1 2.025(2) 5_666 ?
Cu1 O1W 2.485(3) . ?
N1 C2 1.337(2) 2_656 ?
N1 C2 1.337(2) . ?
C2 C2 1.381(4) 6_575 ?
C2 H2 0.9300 . ?
N11 C16 1.353(5) . ?
N11 C12 1.357(5) . ?
N11 H11 0.83(5) . ?
C12 O12 1.265(4) . ?
C12 C13 1.416(5) . ?
C13 C14 1.360(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.495(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17A 0.96(5) 6_565 ?
C17 H17B 0.96(8) 6_565 ?
C17 H17C 0.96(3) 6_565 ?
O1W H1 0.818(17) . ?
O1W H1 0.818(17) 6_565 ?
Cl1 O3A 1.25(3) . ?
Cl1 O3A 1.25(3) 6_575 ?
Cl1 O2 1.390(12) 6_575 ?
Cl1 O2 1.390(12) . ?
Cl1 O1 1.408(4) . ?
Cl1 O2A 1.468(10) 6_575 ?
Cl1 O2A 1.468(10) . ?
Cl1 O3 1.509(15) . ?
Cl1 O3 1.509(15) 6_575 ?
O3 O3 0.77(5) 6_575 ?
O3A O3A 0.80(12) 6_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 Cu1 O12 180.0 . 5_666 ?
O12 Cu1 N1 90.0 . . ?
O12 Cu1 N1 90.0 5_666 . ?
O12 Cu1 N1 90.0 . 5_666 ?
O12 Cu1 N1 90.0 5_666 5_666 ?
N1 Cu1 N1 180.0 . 5_666 ?
O12 Cu1 O1W 84.91(10) . . ?
O12 Cu1 O1W 95.09(10) 5_666 . ?
N1 Cu1 O1W 90.0 . . ?
N1 Cu1 O1W 90.0 5_666 . ?
C2 N1 C2 117.5(2) 2_656 . ?
C2 N1 Cu1 121.27(12) 2_656 . ?
C2 N1 Cu1 121.27(12) . . ?
N1 C2 C2 121.26(12) . 6_575 ?
N1 C2 H2 119.4 . . ?
C2 C2 H2 119.4 6_575 . ?
C16 N11 C12 125.3(3) . . ?
C16 N11 H11 116(3) . . ?
C12 N11 H11 119(3) . . ?
O12 C12 N11 120.8(3) . . ?
O12 C12 C13 123.0(3) . . ?
N11 C12 C13 116.2(3) . . ?
C12 O12 Cu1 137.0(2) . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 122.5(4) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C14 119.1(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
N11 C16 C15 118.0(4) . . ?
N11 C16 C17 116.1(4) . . ?
C15 C16 C17 125.9(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5(11) . 6_565 ?
H17A C17 H17A 124.3 . 6_565 ?
H17B C17 H17A 18.2 . 6_565 ?
H17C C17 H17A 93.0 . 6_565 ?
C16 C17 H17B 109.5(17) . 6_565 ?
H17A C17 H17B 18.2 . 6_565 ?
H17B C17 H17B 93.0 . 6_565 ?
H17C C17 H17B 124.3 . 6_565 ?
H17A C17 H17B 109.5 6_565 6_565 ?
C16 C17 H17C 109.5(7) . 6_565 ?
H17A C17 H17C 93.0 . 6_565 ?
H17B C17 H17C 124.3 . 6_565 ?
H17C C17 H17C 18.2 . 6_565 ?
H17A C17 H17C 109.5 6_565 6_565 ?
H17B C17 H17C 109.5 6_565 6_565 ?
Cu1 O1W H1 120(2) . . ?
Cu1 O1W H1 120(2) . 6_565 ?
H1 O1W H1 114(4) . 6_565 ?
O2 Cl1 O2 121.8(10) 6_575 . ?
O3A Cl1 O1 114.7(14) . . ?
O3A Cl1 O1 114.7(14) 6_575 . ?
O2 Cl1 O1 113.2(6) 6_575 . ?
O2 Cl1 O1 113.2(6) . . ?
O3A Cl1 O2A 102(2) . 6_575 ?
O3A Cl1 O2A 130(2) 6_575 6_575 ?
O2 Cl1 O2A 24.0(5) 6_575 6_575 ?
O2 Cl1 O2A 107.6(4) . 6_575 ?
O1 Cl1 O2A 107.7(4) . 6_575 ?
O3A Cl1 O2A 130(2) . . ?
O3A Cl1 O2A 102(2) 6_575 . ?
O1 Cl1 O2A 107.7(4) . . ?
O2A Cl1 O2A 88.1(6) 6_575 . ?
O2 Cl1 O3 111.4(10) 6_575 . ?
O2 Cl1 O3 85.3(10) . . ?
O1 Cl1 O3 107.9(5) . . ?
O2 Cl1 O3 85.3(10) 6_575 6_575 ?
O2 Cl1 O3 111.4(10) . 6_575 ?
O1 Cl1 O3 107.9(5) . 6_575 ?
O3 Cl1 O3 29.6(19) . 6_575 ?
O3 O3 Cl1 75.2(9) 6_575 . ?
O3A O3A Cl1 71(3) 6_575 . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.066


_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ekdj220
_database_code_depnum_ccdc_archive 'CCDC 2017466'
loop_
_audit_author_name
_audit_author_address
'Matthew Polson'
;Department of Physical and Chemical Sciences, University of Canterbury, Christchurch
New Zealand
;
_audit_update_record             
;
2020-09-05 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;catena-diaquabis(5-methyl-2-pyridone)pyrazinecopper(II) perchlorate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl2 Cu N4 O12'
_chemical_formula_weight         596.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.0161(2)
_cell_length_b                   6.86470(10)
_cell_length_c                   22.3242(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.3680(10)
_cell_angle_gamma                90
_cell_volume                     2297.23(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    219.97(16)
_cell_measurement_reflns_used    12581
_cell_measurement_theta_min      5.8970
_cell_measurement_theta_max      73.4170

_exptl_crystal_description       chunk
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             1220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    4.134
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.43515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      219.97(16)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            21728
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         5.904
_diffrn_reflns_theta_max         73.255
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2305
_reflns_number_gt                2225
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+2.6176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00119(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2305
_refine_ls_number_parameters     171
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.73537(4) 0.250000 0.02076(13) Uani 1 2 d S T P . .
N1 N 0.500000 0.4372(3) 0.250000 0.0211(4) Uani 1 2 d S T P . .
C2 C 0.43684(10) 0.3365(2) 0.21876(7) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.392066 0.403018 0.196666 0.027 Uiso 1 1 calc R U . . .
C3 C 0.43690(10) 0.1338(2) 0.21872(7) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.392224 0.067298 0.196531 0.027 Uiso 1 1 calc R U . . .
N4 N 0.500000 0.0329(3) 0.250000 0.0210(4) Uani 1 2 d S T P . .
N11 N 0.42297(10) 0.6764(2) 0.38809(7) 0.0293(3) Uani 1 1 d . . . . .
H11 H 0.3949(15) 0.652(3) 0.3588(10) 0.035 Uiso 1 1 d . U . . .
C12 C 0.50890(11) 0.7297(2) 0.38401(8) 0.0231(3) Uani 1 1 d . . . . .
O12 O 0.54502(8) 0.73654(16) 0.33361(5) 0.0259(3) Uani 1 1 d . . . . .
C13 C 0.55695(12) 0.7729(3) 0.43886(8) 0.0289(4) Uani 1 1 d . . . . .
H13 H 0.617102 0.805177 0.438980 0.035 Uiso 1 1 calc R U . . .
C14 C 0.51528(13) 0.7672(3) 0.49162(8) 0.0317(4) Uani 1 1 d . . . . .
H14 H 0.547658 0.797307 0.527217 0.038 Uiso 1 1 calc R U . . .
C15 C 0.42418(13) 0.7169(3) 0.49348(8) 0.0317(4) Uani 1 1 d . . . . .
C16 C 0.38098(12) 0.6698(3) 0.44049(8) 0.0339(4) Uani 1 1 d . . . . .
H16 H 0.321434 0.632228 0.439883 0.041 Uiso 1 1 calc R U . . .
C17 C 0.37839(17) 0.7138(3) 0.55156(10) 0.0453(5) Uani 1 1 d . . . . .
H17A H 0.357753 0.842427 0.560367 0.054 Uiso 1 1 calc R U . . .
H17B H 0.419630 0.670818 0.583314 0.054 Uiso 1 1 calc R U . . .
H17C H 0.328524 0.626166 0.548086 0.054 Uiso 1 1 calc R U . . .
O1W O 0.34607(9) 0.74423(19) 0.27113(6) 0.0303(3) Uani 1 1 d D . . . .
H1A H 0.3215(14) 0.840(3) 0.2825(10) 0.036 Uiso 1 1 d D U . . .
H1B H 0.3119(14) 0.709(3) 0.2443(9) 0.036 Uiso 1 1 d D U . . .
Cl1 Cl 0.30378(3) 1.20057(7) 0.36430(2) 0.03205(14) Uani 1 1 d . . . . .
O1 O 0.25922(10) 1.0560(2) 0.32566(8) 0.0587(5) Uani 1 1 d . . . . .
O2 O 0.39782(9) 1.1850(3) 0.36053(7) 0.0588(5) Uani 1 1 d . . . . .
O3 O 0.28182(11) 1.1719(4) 0.42443(8) 0.0673(5) Uani 1 1 d . . . . .
O4 O 0.27281(13) 1.3867(3) 0.34458(10) 0.0736(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O12 1.9475(12) . ?
Cu1 O12 1.9475(12) 2_655 ?
Cu1 N4 2.0427(19) 1_565 ?
Cu1 N1 2.0467(18) . ?
Cu1 O1W 2.3868(13) . ?
Cu1 O1W 2.3869(13) 2_655 ?
N1 C2 1.3366(18) 2_655 ?
N1 C2 1.3366(18) . ?
C2 C3 1.391(2) . ?
C3 N4 1.3368(18) . ?
N11 C12 1.349(2) . ?
N11 C16 1.362(2) . ?
C12 O12 1.278(2) . ?
C12 C13 1.415(2) . ?
C13 C14 1.366(3) . ?
C14 C15 1.414(3) . ?
C15 C16 1.354(3) . ?
C15 C17 1.503(3) . ?
Cl1 O3 1.4147(17) . ?
Cl1 O4 1.4209(18) . ?
Cl1 O2 1.4236(15) . ?
Cl1 O1 1.4523(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 Cu1 O12 179.53(7) . 2_655 ?
O12 Cu1 N4 89.76(3) . 1_565 ?
O12 Cu1 N4 89.76(3) 2_655 1_565 ?
O12 Cu1 N1 90.24(3) . . ?
O12 Cu1 N1 90.24(3) 2_655 . ?
N4 Cu1 N1 180.0 1_565 . ?
O12 Cu1 O1W 95.52(5) . . ?
O12 Cu1 O1W 84.47(5) 2_655 . ?
N4 Cu1 O1W 88.54(3) 1_565 . ?
N1 Cu1 O1W 91.46(3) . . ?
O12 Cu1 O1W 84.47(5) . 2_655 ?
O12 Cu1 O1W 95.52(5) 2_655 2_655 ?
N4 Cu1 O1W 88.54(3) 1_565 2_655 ?
N1 Cu1 O1W 91.46(3) . 2_655 ?
O1W Cu1 O1W 177.08(6) . 2_655 ?
C2 N1 C2 117.68(19) 2_655 . ?
C2 N1 Cu1 121.16(10) 2_655 . ?
C2 N1 Cu1 121.16(10) . . ?
N1 C2 C3 121.15(14) . . ?
N4 C3 C2 121.21(14) . . ?
C3 N4 C3 117.61(19) . 2_655 ?
C3 N4 Cu1 121.20(10) . 1_545 ?
C3 N4 Cu1 121.20(10) 2_655 1_545 ?
C12 N11 C16 124.02(16) . . ?
O12 C12 N11 121.74(15) . . ?
O12 C12 C13 122.18(16) . . ?
N11 C12 C13 116.06(16) . . ?
C12 O12 Cu1 134.59(11) . . ?
C14 C13 C12 120.26(17) . . ?
C13 C14 C15 121.66(17) . . ?
C16 C15 C14 116.57(17) . . ?
C16 C15 C17 122.01(19) . . ?
C14 C15 C17 121.41(18) . . ?
C15 C16 N11 121.35(17) . . ?
O3 Cl1 O4 109.19(14) . . ?
O3 Cl1 O2 109.45(10) . . ?
O4 Cl1 O2 110.93(13) . . ?
O3 Cl1 O1 110.09(12) . . ?
O4 Cl1 O1 107.44(11) . . ?
O2 Cl1 O1 109.72(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C2 C3 -0.06(10) 2_655 . . . ?
Cu1 N1 C2 C3 179.94(10) . . . . ?
N1 C2 C3 N4 0.1(2) . . . . ?
C2 C3 N4 C3 -0.06(10) . . . 2_655 ?
C2 C3 N4 Cu1 179.94(10) . . . 1_545 ?
C16 N11 C12 O12 -178.89(16) . . . . ?
C16 N11 C12 C13 2.6(3) . . . . ?
N11 C12 O12 Cu1 14.9(2) . . . . ?
C13 C12 O12 Cu1 -166.71(12) . . . . ?
O12 C12 C13 C14 178.80(15) . . . . ?
N11 C12 C13 C14 -2.7(2) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 1.6(3) . . . . ?
C13 C14 C15 C17 -179.09(18) . . . . ?
C14 C15 C16 N11 -1.8(3) . . . . ?
C17 C15 C16 N11 178.90(18) . . . . ?
C12 N11 C16 C15 -0.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H11 O1W 0.78(2) 2.14(2) 2.831(2) 148(2) . yes
N11 H11 O4 0.78(2) 2.59(2) 3.118(2) 127(2) 1_545 yes
O1W H1A O1 0.804(16) 2.025(17) 2.819(2) 170(2) . yes
O1W H1B Cl1 0.803(16) 2.899(17) 3.6734(14) 163(2) 4_545 yes
O1W H1B O1 0.803(16) 2.117(17) 2.905(2) 167(2) 4_545 yes

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.056


_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ekdj120
_database_code_depnum_ccdc_archive 'CCDC 2017467'
loop_
_audit_author_name
_audit_author_address
'Matthew Polson'
;Department of Physical and Chemical Sciences, University of Canterbury, Christchurch
New Zealand
;
_audit_update_record             
;
2020-07-19 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'catena-diaquabis(5-methyl-2-pyridone)pyrazinecopper(II) perchlorate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl2 Cu N4 O12'
_chemical_formula_weight         596.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8463(3)
_cell_length_b                   8.0507(5)
_cell_length_c                   11.6595(6)
_cell_angle_alpha                79.958(5)
_cell_angle_beta                 73.894(4)
_cell_angle_gamma                66.235(5)
_cell_volume                     563.63(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    120.01(16)
_cell_measurement_reflns_used    6825
_cell_measurement_theta_min      5.9710
_cell_measurement_theta_max      73.3430

_exptl_crystal_description       chunk
_exptl_crystal_colour            blue-green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             305
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .63
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    4.212
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.50770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      120.01(16)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10703
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         6.021
_diffrn_reflns_theta_max         73.497
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2214
_reflns_number_gt                2175
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0821P)²+1.7947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2214
_refine_ls_number_parameters     170
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1677
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_restrained_S_all      1.254
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
CU1 Cu 0.500000 0.500000 0.500000 0.0131(3) Uani 1 2 d S . P . .
N1 N 0.7936(5) 0.5044(4) 0.5024(3) 0.0129(6) Uani 1 1 d . . . . .
C2 C 0.8669(6) 0.6327(5) 0.4379(3) 0.0148(7) Uani 1 1 d . . . . .
H2 H 0.778257 0.725889 0.394022 0.018 Uiso 1 1 calc R U . . .
C6 C 0.9270(6) 0.3727(5) 0.5638(3) 0.0146(7) Uani 1 1 d . . . . .
H6 H 0.880622 0.282475 0.608853 0.018 Uiso 1 1 calc R U . . .
N11 N 0.6344(6) 0.3430(5) 0.2305(3) 0.0176(7) Uani 1 1 d . . . . .
H11 H 0.597(8) 0.284(7) 0.303(5) 0.021 Uiso 1 1 d . U . . .
C12 C 0.6113(6) 0.5176(5) 0.2341(3) 0.0147(7) Uani 1 1 d . . . . .
O12 O 0.5406(4) 0.5927(4) 0.3330(2) 0.0166(6) Uani 1 1 d . . . . .
C13 C 0.6643(6) 0.6112(5) 0.1226(4) 0.0186(8) Uani 1 1 d . . . . .
H13 H 0.642962 0.733346 0.119734 0.022 Uiso 1 1 calc R U . . .
C14 C 0.7463(7) 0.5238(6) 0.0191(4) 0.0192(8) Uani 1 1 d . . . . .
H14 H 0.782617 0.587061 -0.052974 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7771(7) 0.3388(6) 0.0195(4) 0.0197(8) Uani 1 1 d . . . . .
C16 C 0.7159(7) 0.2540(6) 0.1271(4) 0.0189(8) Uani 1 1 d . . . . .
H16 H 0.729707 0.133621 0.130517 0.023 Uiso 1 1 calc R U . . .
C17 C 0.8717(8) 0.2414(7) -0.0941(4) 0.0261(9) Uani 1 1 d . . . . .
H17A H 1.027275 0.211288 -0.116611 0.031 Uiso 1 1 calc R U . . .
H17B H 0.805994 0.318807 -0.156695 0.031 Uiso 1 1 calc R U . . .
H17C H 0.842050 0.131915 -0.081285 0.031 Uiso 1 1 calc R U . . .
O1W O 0.3284(5) 0.8149(4) 0.5366(2) 0.0181(6) Uani 1 1 d D . . . .
H1A H 0.192(3) 0.868(7) 0.561(5) 0.022 Uiso 1 1 d D U . . .
H1B H 0.357(8) 0.880(6) 0.476(3) 0.022 Uiso 1 1 d D U . . .
CL1 Cl -0.24415(15) 0.88402(12) 0.73240(8) 0.0179(3) Uani 1 1 d . . . . .
O1 O -0.4150(6) 0.9445(5) 0.6663(3) 0.0296(7) Uani 1 1 d . . . . .
O2 O -0.0945(5) 0.9773(4) 0.6770(3) 0.0250(7) Uani 1 1 d . . . . .
O3 O -0.1268(6) 0.6914(4) 0.7262(3) 0.0284(7) Uani 1 1 d . . . . .
O4 O -0.3396(5) 0.9281(4) 0.8541(3) 0.0274(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
CU1 O12 1.946(3) . ?
CU1 O12 1.946(3) 2_666 ?
CU1 N1 2.032(3) 2_666 ?
CU1 N1 2.032(3) . ?
CU1 O1W 2.385(3) 2_666 ?
CU1 O1W 2.385(3) . ?
N1 C6 1.338(5) . ?
N1 C2 1.350(5) . ?
C2 C6 1.388(5) 2_766 ?
C6 C2 1.388(5) 2_766 ?
N11 C12 1.357(5) . ?
N11 C16 1.373(5) . ?
C12 O12 1.276(5) . ?
C12 C13 1.417(6) . ?
C13 C14 1.366(6) . ?
C14 C15 1.417(6) . ?
C15 C16 1.362(6) . ?
C15 C17 1.504(6) . ?
CL1 O4 1.429(3) . ?
CL1 O3 1.435(3) . ?
CL1 O1 1.453(3) . ?
CL1 O2 1.454(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 CU1 O12 180.0 . 2_666 ?
O12 CU1 N1 90.67(12) . 2_666 ?
O12 CU1 N1 89.33(12) 2_666 2_666 ?
O12 CU1 N1 89.33(12) . . ?
O12 CU1 N1 90.67(12) 2_666 . ?
N1 CU1 N1 180.00(17) 2_666 . ?
O12 CU1 O1W 96.51(10) . 2_666 ?
O12 CU1 O1W 83.49(10) 2_666 2_666 ?
N1 CU1 O1W 89.75(11) 2_666 2_666 ?
N1 CU1 O1W 90.26(11) . 2_666 ?
O12 CU1 O1W 83.49(10) . . ?
O12 CU1 O1W 96.51(10) 2_666 . ?
N1 CU1 O1W 90.25(11) 2_666 . ?
N1 CU1 O1W 89.74(11) . . ?
O1W CU1 O1W 180.00(14) 2_666 . ?
C6 N1 C2 117.4(3) . . ?
C6 N1 CU1 120.5(3) . . ?
C2 N1 CU1 122.0(3) . . ?
N1 C2 C6 120.9(4) . 2_766 ?
N1 C6 C2 121.7(3) . 2_766 ?
C12 N11 C16 123.4(4) . . ?
O12 C12 N11 121.1(4) . . ?
O12 C12 C13 122.6(4) . . ?
N11 C12 C13 116.3(3) . . ?
C12 O12 CU1 133.6(3) . . ?
C14 C13 C12 120.6(4) . . ?
C13 C14 C15 121.4(4) . . ?
C16 C15 C14 116.9(4) . . ?
C16 C15 C17 121.7(4) . . ?
C14 C15 C17 121.4(4) . . ?
C15 C16 N11 121.2(4) . . ?
O4 CL1 O3 110.36(19) . . ?
O4 CL1 O1 109.7(2) . . ?
O3 CL1 O1 109.5(2) . . ?
O4 CL1 O2 109.81(19) . . ?
O3 CL1 O2 109.35(19) . . ?
O1 CL1 O2 108.03(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C6 -0.2(6) . . . 2_766 ?
CU1 N1 C2 C6 -176.6(3) . . . 2_766 ?
C2 N1 C6 C2 0.2(6) . . . 2_766 ?
CU1 N1 C6 C2 176.7(3) . . . 2_766 ?
C16 N11 C12 O12 -178.0(3) . . . . ?
C16 N11 C12 C13 3.7(6) . . . . ?
N11 C12 O12 CU1 14.0(5) . . . . ?
C13 C12 O12 CU1 -167.7(3) . . . . ?
O12 C12 C13 C14 177.9(4) . . . . ?
N11 C12 C13 C14 -3.8(6) . . . . ?
C12 C13 C14 C15 1.2(6) . . . . ?
C13 C14 C15 C16 1.6(6) . . . . ?
C13 C14 C15 C17 -178.7(4) . . . . ?
C14 C15 C16 N11 -1.9(6) . . . . ?
C17 C15 C16 N11 178.5(4) . . . . ?
C12 N11 C16 C15 -0.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O2_$1 0.93 2.40 3.271(5) 156.3 1_645
N11 H11 O1W_$2 0.92(6) 2.02(6) 2.823(5) 145(4) 2_666
N11 H11 O1_$3 0.92(6) 2.53(5) 3.144(5) 125(4) 2_566
O1W H1A O2 0.84(2) 2.00(3) 2.799(4) 158(5) .
O1W H1B CL1_$4 0.83(2) 2.89(3) 3.643(3) 151(4) 2_576
O1W H1B O1_$4 0.83(2) 2.04(2) 2.873(4) 176(5) 2_576

_refine_diff_density_max         2.587
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.137

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ekdoa_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2017465'
loop_
_audit_author_name
_audit_author_address
'Matthew Polson'
;Department of Physical and Chemical Sciences, University of Canterbury, Christchurch
New Zealand
;
_audit_update_record             
;
2020-07-19 deposited with the CCDC.	2020-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 Cl2 Cu N4 O12'
_chemical_formula_weight         596.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8314(6)
_cell_length_b                   8.1609(9)
_cell_length_c                   10.4545(10)
_cell_angle_alpha                90.984(8)
_cell_angle_beta                 99.500(7)
_cell_angle_gamma                93.911(8)
_cell_volume                     573.28(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    280.00(10)
_cell_measurement_reflns_used    1876
_cell_measurement_theta_min      3.8440
_cell_measurement_theta_max      28.8270

_exptl_crystal_description       prism
_exptl_crystal_colour            blue-green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             305
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    1.256
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.437
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      280.00(10)
_diffrn_ambient_environment      air
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            5016
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.332
_diffrn_reflns_theta_max         30.708
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.811
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             5016
_reflns_number_gt                3882
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHelxl-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1312P)²+0.1365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5016
_refine_ls_number_parameters     207
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2306
_refine_ls_wR_factor_gt          0.2060
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.500000 0.500000 0.500000 0.0336(3) Uani 1 2 d S . P . .
N1 N -0.1980(5) 0.4993(4) 0.4997(3) 0.0240(7) Uani 1 1 d . . . . .
C2 C -0.0925(7) 0.3907(6) 0.5672(4) 0.0329(10) Uani 1 1 d . . . . .
H2 H -0.154450 0.312990 0.614139 0.039 Uiso 1 1 calc R U . . .
C3 C -0.1100(7) 0.6075(6) 0.4321(4) 0.0329(10) Uani 1 1 d . . . . .
H3 H -0.184458 0.683042 0.383518 0.039 Uiso 1 1 calc R U . . .
N11 N -0.3465(8) 0.6478(6) 0.8076(5) 0.0470(12) Uani 1 1 d . . . . .
H11 H -0.380(11) 0.707(8) 0.746(6) 0.056 Uiso 1 1 d . U . . .
C12 C -0.3794(7) 0.4838(6) 0.7882(5) 0.0347(11) Uani 1 1 d . . . . .
O12 O -0.4621(5) 0.4240(5) 0.6769(3) 0.0376(8) Uani 1 1 d . . . . .
C13 C -0.3215(8) 0.3830(7) 0.8952(5) 0.0372(11) Uani 1 1 d . . . . .
C14 C -0.2420(9) 0.4601(8) 1.0111(5) 0.0471(14) Uani 1 1 d . . . . .
H14 H -0.204947 0.396336 1.082716 0.057 Uiso 1 1 calc R U . . .
C15 C -0.2146(10) 0.6298(9) 1.0259(6) 0.0553(16) Uani 1 1 d . . . . .
H15 H -0.161175 0.678563 1.106262 0.066 Uiso 1 1 calc R U . . .
C16 C -0.2653(10) 0.7214(8) 0.9242(6) 0.0545(16) Uani 1 1 d . . . . .
H16 H -0.245800 0.835247 0.932193 0.065 Uiso 1 1 calc R U . . .
C17 C -0.3478(11) 0.2021(8) 0.8752(6) 0.0538(15) Uani 1 1 d . . . . .
H17A H -0.256401 0.167218 0.821417 0.065 Uiso 1 1 calc R U . . .
H17B H -0.481658 0.171322 0.833688 0.065 Uiso 1 1 calc R U . . .
H17C H -0.322369 0.150549 0.957565 0.065 Uiso 1 1 calc R U . . .
O1W O -0.4546(7) 0.7976(5) 0.5661(4) 0.0527(10) Uani 1 1 d D . . . .
H1A H -0.546(8) 0.862(7) 0.569(6) 0.063 Uiso 1 1 d D U . . .
H1B H -0.349(7) 0.855(8) 0.565(6) 0.063 Uiso 1 1 d D U . . .
Cl1 Cl 0.1214(3) 0.93275(18) 0.70919(14) 0.0554(5) Uani 1 1 d . . . . .
O1 O -0.005(4) 0.806(3) 0.671(2) 0.106(9) Uani 0.449(15) 1 d . . P A 1
O2 O 0.289(3) 0.882(3) 0.7959(14) 0.120(8) Uani 0.449(15) 1 d . . P A 1
O3 O 0.068(3) 1.0745(17) 0.7441(17) 0.113(8) Uani 0.449(15) 1 d . . P A 1
O4 O 0.258(4) 1.005(3) 0.645(2) 0.069(5) Uani 0.449(15) 1 d . . P A 1
O1' O 0.094(3) 0.7604(19) 0.7117(18) 0.092(6) Uani 0.551(15) 1 d . . P A 2
O2' O 0.146(2) 0.9932(17) 0.8430(11) 0.105(6) Uani 0.551(15) 1 d . . P A 2
O3' O -0.0852(15) 0.9858(17) 0.6611(11) 0.092(5) Uani 0.551(15) 1 d . . P A 2
O4' O 0.220(3) 0.966(3) 0.5920(19) 0.074(5) Uani 0.551(15) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O12 1.943(3) 2_466 ?
Cu1 O12 1.943(3) . ?
Cu1 N1 2.064(4) . ?
Cu1 N1 2.064(4) 2_466 ?
N1 C3 1.315(6) . ?
N1 C2 1.321(6) . ?
C2 C3 1.381(6) 2_566 ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
N11 C12 1.349(7) . ?
N11 C16 1.364(7) . ?
N11 H11 0.82(7) . ?
C12 O12 1.279(6) . ?
C12 C13 1.419(7) . ?
C13 C14 1.367(7) . ?
C13 C17 1.482(9) . ?
C14 C15 1.388(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.323(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O1W H1A 0.84(3) . ?
O1W H1B 0.84(3) . ?
Cl1 O3 1.300(13) . ?
Cl1 O1 1.312(17) . ?
Cl1 O4 1.35(3) . ?
Cl1 O1' 1.407(16) . ?
Cl1 O2 1.431(15) . ?
Cl1 O2' 1.455(10) . ?
Cl1 O3' 1.512(10) . ?
Cl1 O4' 1.51(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 Cu1 O12 180.0 2_466 . ?
O12 Cu1 N1 89.85(14) 2_466 . ?
O12 Cu1 N1 90.15(14) . . ?
O12 Cu1 N1 90.15(14) 2_466 2_466 ?
O12 Cu1 N1 89.85(14) . 2_466 ?
N1 Cu1 N1 180.0 . 2_466 ?
C3 N1 C2 119.8(4) . . ?
C3 N1 Cu1 119.9(3) . . ?
C2 N1 Cu1 120.3(3) . . ?
N1 C2 C3 119.9(4) . 2_566 ?
N1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 2_566 . ?
N1 C3 C2 120.3(4) . 2_566 ?
N1 C3 H3 119.9 . . ?
C2 C3 H3 119.9 2_566 . ?
C12 N11 C16 123.7(5) . . ?
C12 N11 H11 118(5) . . ?
C16 N11 H11 118(5) . . ?
O12 C12 N11 120.2(5) . . ?
O12 C12 C13 122.2(5) . . ?
N11 C12 C13 117.6(5) . . ?
C12 O12 Cu1 135.9(3) . . ?
C14 C13 C12 117.4(5) . . ?
C14 C13 C17 123.9(5) . . ?
C12 C13 C17 118.8(5) . . ?
C13 C14 C15 122.5(6) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C16 C15 C14 119.1(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 N11 119.6(6) . . ?
C15 C16 H16 120.2 . . ?
N11 C16 H16 120.2 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H1A O1W H1B 108(7) . . ?
O3 Cl1 O1 123.5(16) . . ?
O3 Cl1 O4 91.5(14) . . ?
O1 Cl1 O4 127.9(13) . . ?
O3 Cl1 O2 112.0(13) . . ?
O1 Cl1 O2 110.4(14) . . ?
O4 Cl1 O2 84.9(13) . . ?
O1' Cl1 O2' 106.8(10) . . ?
O1' Cl1 O3' 103.8(10) . . ?
O2' Cl1 O3' 99.2(8) . . ?
O1' Cl1 O4' 104.9(12) . . ?
O2' Cl1 O4' 136.9(10) . . ?
O3' Cl1 O4' 100.8(10) . . ?

_refine_diff_density_max         2.708
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.180


_exptl_crystal_preparation       'Magnetic properties'
